In 1922, people of the Quaker Oats Company were able to commercialize furfural production by treating oat hulls

from their cereal mill in Cedar Rapids, Iowa. Since decades, annually harvested agro-wastes like corn cobs, sugar
cane bagasse,
cereal byproducts or pulping wastes make up a bottomless renewable feedstock for furfural production.

The worldwide leading manufacturer of this renewable chemical, Central Romana Corporation is located in the
Dominican Republic. Bagasse, left over from sugar cane processing, is valorized for furfural production.

International Furan Chemicals has the exclusive use and distribution rights of the Central Romana Corporation
furfural
output of some 35,000 tons.

Furfural has an aromatic odor reminiscent of almonds. Its exceptional physical properties make from this hetero-
aromaticaldehyde a selective solvent for refining lubricating oils. In the manufacture of resin-bonded grinding wheels
and refractory materials this biomass based chemical is used at the same time as a reactive chemical and as solvent.

Furfural is the sole industrial source for furfuryl alcohol, tetrahydrofurfuryl alcohol, furoic acid, furfurylamine,
methylfuran
and furan. Without hesitation furfuryl alcohol is its principal derivative. Since the sixties and seventies furfuryl alcohol
resins replace oil based binders in the foundry industry.
Naturally occurring and readily replenishable agricultural residues like sugar cane bagasse (a byproduct of sugar
cane harvesting), corn cobs, wood products or cereal byproducts such as the hulls of cotton seed, oats and rice make
up a huge renewable feedstock for furfural production. These hemicellulosic agricultural wastes are all rich in
pentosans, the precursor polysaccharide of furfural.

Furfural is produced in a digester under high-pressure steam, from where it is recovered by steam distillation,
followed by water-furfural separation and purification. The scheme illustrates all consecutive steps in the conversion
of sugar cane bagasse into Furfural. In the first step pentosans are hydrolyzed by strong mineral acids to monomeric
C5-sugars. Subsequent cyclodehydration of the pentoses yields Furfural.

  Sugar Cane
    Furfural Processing
Processing

I. Cane preparation
II. Extraction Sugar Cane Bagasse
III. Juice clarification
I. Hydrolysis (H+,H2O)
Juice
IV. Cyclodehydration
concentration II.
(H+,-3H2O)
Crystallisation and
V. III. Steam Destillation
Separation
Separation
VI. Refining IV.
(H2O/Furfural)
  V. Purification

Sugarcane Sucrose Furfural

Hemicelluloses [1] are, next to cellulose, the second most abundant natural organic chemicals in the biosphere,
present in all parts of the plant, concentrated in the primary and secondary layers of the cell wall and closely
associated with cellulose and lignin. Their biological function is as connecting or integrating units. The chief
constituent of this fraction is xylan, a polysaccharide with backbone chains of (1'4)-linked b-D-xylopyranosyl residues.
Roughly speaking, the main constituents of the hetero-polysaccharides in hemicellulose are D-xylose and L-
arabinose.
Furfural

Furfural, G.C. Assay, % 99 min

Moisture, wt % 0.2 max

Acidity, mEq/l 20 max

Residue, wt % 0.5 max

General Properties

Molecular weight 96.08

Boiling point at 101.3 kPa (1 atm), °C 161.7

Freezing point, °C -36.5

Refractive index, nD

1.5261
 20°C
1.5235
 25°C

Density, d4 at 20°C, g/cm3 1.1598

Vapor pressure Download as pdf-document

Vapor density (air=1) 3.3

Critical pressure, Pc, MPa 5.502

Critical temperature, Tc, °C 397

Gibb's free energy of formation  

Solubility in, wt% Download as pdf-document

 water 8.3

alcohol; ether 8

Thermodynamic Properties

Heat of vaporization (liq), kJ/mol 42.8

Heat capacity (liq), J/(g.K)

1.74
20-100°C

Heat of combustion (liq), kJ/mol 2344

Enthalpy of formation   

Fluid Properties

Viscosity, mPa.s, 25°C 1.49

Surface tension, mN/m (=dyn/cm)  

29.9°C 40.7

Electrical Properties

Dielectric constant 20°C 41.9

Flammability Properties

Explosion limits (in air), vol% 2.1-19.3

Flash point, °C, tag closed cup 61.7

Auto ignition temperature, °C 315

refining of lubricating oils & decolorizing agent

Furfural thanks several large scale applications to its solubility characteristics and its easy recuperation by steam
distillation. Furfural has the unique property to dissolve aromatics and other unsaturated olefins. Today all major oil
companies use furfural as selective solvent in the refining of lubricating oils. The first refining unit was built by a
subsidiary of Texaco, the Indian Refining Company. This technology lead to production of high quality motor oil with
improved temperature-viscosity properties. Aromatics, polar components, mercaptans are removed from petroleum
by means of furfural extraction. Furfural can also be used as decolorizing agent to refine crude wood rosin.
purification technology for C4 and C5 hydrocarbons

During the Second World War the purification technology of butadiene was developed in the United States for the
manufacture of synthetic rubber. By extractive distillation with furfural butadiene or isoprene can be separated from
other C4 and C5 hydrocarbons, respectively.

reactive solvent and good wetting agent

Furfural is unusually effective as a solvent for phenolic resins. In the manufacture of abrasive wheels, brake linings
and refractory products for the steel industry furfural is known as a reactive solvent and excellent wetting agent.

unique chemical feedstock for other furan derivatives

However, the main outlet of furfural is as chemical feedstock for the production of furfuryl alcohol and for other 5-
membered oxygen-containing heterocycles, i.e. furan, methylfuran, acetylfuran, furfurylamine and furoic acid.

Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four
carbon atoms and one oxygen. The class of compounds containing such rings are also referred to as
furans. The parent compound is typically derived by the thermal decomposition of pentose-containing
materials, cellulosic solids especially pine-wood. Furan is a colorless, flammable, highly volatile liquid
with a boiling point close to room temperature. It is toxic and may be carcinogenic. Catalytic
hydrogenation (see redox) of furan with a palladium catalyst gives tetrahydrofuran.

Heterocyclic compounds are cyclic compounds with at least two different elements as ring members
atoms eg: pyridine

Thermal decomposition, also called thermolysis, is defined as a chemical reaction in which a

compound breaks up into at least two other substances when heated. The reaction is usually
endothermic as heat is required to break chemical bonds in the compound undergoing
decomposition. The decomposition temperature of a substance is the temperature at which the
substance decomposes into smaller substances or into its constituent atoms. When this takes place it
needs to be supervised as it can be dangerous

For example, calcium carbonate decomposes into calcium oxide and carbon dioxide when
heated:

CaCO3 → CaO + CO2

History

The name furan comes from the Latin furfur, which means bran.[1] The first furan derivative to be
described was 2-furoic acid, by Carl Wilhelm Scheele in 1780. Another important derivative, furfural,
was reported by Johann Wolfgang Döbereiner in 1831 and characterised nine years later by John
Stenhouse. Furan itself was first prepared by Heinrich Limpricht in 1870, although he called it
tetraphenol.[2][3] .

Synthesis and isolation

 Furan can be obtained from furfural by oxidation and decarboxylation of the resulting furan-2-
carboxylic acid, the furfural being derived by destructive distillation of corn cobs in the presence
of sulfuric acid.[4]
 A classic furan organic synthesis is the Feist-Benary synthesis.
 One of the most simple synthesis methods for furans is the reaction of 1,4-diketones with
phosphorus pentoxide (P2O5) in the Paal-Knorr Synthesis. It is interesting that the thiophene
formation reaction of 1,4-diketones with Lawesson's reagent also forms furans as side
products.

Chemistry

Furan is aromatic because one of the lone pairs of electrons on the oxygen atom is
delocalized into the ring, creating a 4n+2 aromatic system (see Hückel's rule) similar to
benzene. Because of the aromaticity, the molecule is flat and lacks discrete double bonds. The
other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system. The
sp2 hybridization is to allow one of the lone pairs of oxygen to reside in a p orbital and thus
allow it to interact within the pi-system.

Due to its aromaticity, furan's behavior is quite dissimilar to that of the more typical heterocyclic
ethers such as tetrahydrofuran.

 It is considerably more reactive than benzene in electrophilic substitution reactions, due to

the electron-donating effects of the oxygen heteroatom. Examination of the resonance
contributors shows the increased electron density of the ring, leading to increased rates of
electrophilic substitution[5].

(In chemistry, delocalized electrons are electrons in a molecule that are not associated with a single
atom or one covalent bond. [1] Delocalized electrons are contained within an orbital that extends over
several adjacent atoms)
 Properties

Molecular formula C4H4O

Molar mass 68.07 g/mol

Appearance colorless, volatile liquid

Density 0.936 g/mL

Melting point -85.6 °C

Boiling point 31.4 °C

Hazards

Flash point -35 °C

Related compounds

Pyrrole
Related heterocycles
Thiophene

Tetrahydrofuran (THF)
2,5-Dimethylfuran
Related compounds
Benzofuran
Dibenzofuran

   (what is this?)  (verify)
Except where noted otherwise, data are given for materials
in their standard state (at 25 °C, 100 kPa)

Infobox references
Typical Uses:

1.Corrosion resistant mortar cements

2.Impregnation (brake linings, abrasives, graphite)

3.Sand/soil consolidation

4.Molding compounds

5.Component in wire insulation compositions

Storage Conditions:

Optimum storage conditions are between 40° and 75°F.

Applications:

In the case of a filled resin system, such as mortar cements, solid acid
catalysts may be ground or

dispersed in the filler, and the acid/filler mixed with the resin at the
time of use. Aqueous or

alcoholic solutions may be used when liquid catalysts are desired.